| Date & Time | Game | Venue |
|---|---|---|
| December 08, 2018 | (2) Ashland Clockers at (2) Westwood Wolverines | Canton Ice House |
| December 15, 2018 | (2) Westwood Wolverines at (1) Norwood Mustangs | Rodman Arena |
| December 19, 2018 | (4) Westwood Wolverines at (0) Holliston Panthers | Blackstone Valley Ice Arena |
| December 22, 2018 | (1) Dedham Marauders at (9) Westwood Wolverines | Canton Ice House |
| December 29, 2018 | (0) Westwood Wolverines at (4) Canton Bulldogs
Joe Donnelly Cup |
Canton Ice House |
| January 05, 2019 | (3) Hopkinton Hillers at (3) Westwood Wolverines | Canton Ice House |
| January 09, 2019 | (6) Westwood Wolverines at (0) Norton Lancers | Foxboro Sports Center |
| January 12, 2019 | (1) Westwood Wolverines at (1) Medfield Warriors | Pirelli Veterans Arena |
| January 16, 2019 | (3) Westwood Wolverines at (2) Shrewsbury Colonials | NorthStar Ice Sports |
| January 19, 2019 | (5) Westwood Wolverines at (5) Ashland Clockers | Loring Arena |
| January 23, 2019 | (2) Dover-Sherborn/Weston Raiders at (3) Westwood Wolverines | Canton Ice House |
| January 26, 2019 | (2) Norwood Mustangs at (2) Westwood Wolverines | Canton Ice House |
| January 30, 2019 | (1) Holliston Panthers at (5) Westwood Wolverines | Canton Ice House |
| February 02, 2019 | (9) Westwood Wolverines at (2) Bellingham Blackhawks | Pirelli Veterans Arena |
| February 06, 2019 | (4) Westwood Wolverines at (3) Hopkinton Hillers | Navin Arena |
| February 09, 2019 | (1) Medway Mustangs at (2) Westwood Wolverines | Canton Ice House |
| February 13, 2019 | (1) Medfield Warriors at (3) Westwood Wolverines | Canton Ice House |
| February 16, 2019 | (0) Lynnfield Pioneers at (0) Westwood Wolverines | Canton Ice House |
| February 18, 2019 | (1) Oliver Ames Tigers at (6) Westwood Wolverines | Canton Ice House |
| February 20, 2019 | (3) Westwood Wolverines at (0) Bourne Canalmen | Gallo Arena |
| February 26, 2019 | (1) Whitman-Hanson Panthers at (5) Westwood Wolverines | Canton Ice House |
| March 02, 2019 | (1) Bishop Feehan Shamrocks at (2) Westwood Wolverines | Canton Ice House |
| March 05, 2019 | (3) Westwood Wolverines at (2) Medfield Warriors | Gallo Arena |
| March 10, 2019 | (8) Canton Bulldogs at (0) Westwood Wolverines | Gallo Arena |
